


Take a Chance

by hornsbeforehalos



Category: Supernatural
Genre: Demon Dean Winchester, F/M, Smut
Language: English
Status: Completed
Published: 2018-12-05
Updated: 2018-12-05
Packaged: 2019-09-12 07:57:44
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,154
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16869121
Author URL: https://archiveofourown.org/users/hornsbeforehalos/pseuds/hornsbeforehalos
Summary: She kept her head down as she watched him from the veil of blonde hair covering her face, calculating his body language and hoping to spot some form of weakness. Of course he didn’t have one, though, he was a Winchester.





	Take a Chance

**Author's Note:**

> *I do not own Supernatural or any of it’s characters. I just play with them.  
> ~DO NOT REPOST MY WORK ANYWHERE. I WILL FIND YOU  
> Written for my 500 follower's contest winner, @pink1031

She recognized him the moment he sauntered into the bar like he owned the place, the Devilish smirk sprawled across his face showing off those Winchester Dimples and giving him away instantly. She’d been expecting him, knew he’d be there at that particular bar at that particular time, but now that the time was upon her, she really didn’t know what the fuck she was gonna do. 

Crowley had had her looking for him since he disappeared, in payment for a debt that she owed him. She’d always made it seem like she knew what she was doing, and had taken care of simple jobs for him with what appeared to be ease. Little did he know, though, that she was constantly scared absolutely shitless by the monsters and demons he sent her after, and it was generally only by  _chance_ that she managed to stay alive and get the job done. 

So now that she was sitting in a booth and eyeing probably the most dangerous thing that had ever walked the planet, she wondered if just letting the King of Hell kill her was such a bad idea after all. She ordered another round of liquid courage when the waitress approached, keeping the demonic man in her peripheral as she spoke to the other woman. She could have sworn she saw him turn his head towards her, but she chocked it up to her nerves as she smiled at the girl who returned with her drinks. 

 

* * *

 

She stayed there for hours, watching him, waiting for him to make any sort of move that could potentially give her an advantage. She really wasn’t sure how Crowley expected her to actually  _capture_  the man; it’s not like she could just bust out the spray paint from her backpack and paint a sigil and be inconspicuous. 

She kept her head down as she watched him from the veil of blonde hair covering her face, calculating his body language and hoping to spot some form of weakness. Of course he didn’t have one, though, he was a  _Winchester._

The waitress came by again, with a new shot glass that was full of what looked like whiskey, and a smirk on her face. She slid it onto the top of the table with a wink, “The handsome gentleman at the bar would like to say hello.” 

Gulping as anxiety rose through her nervous system, her eyes darted to where Dean was sitting, looking over his shoulder at her as he raised his own glass. She whimpered a smile back herself, raising the glass before downing the liquid as they kept their eyes trained on each other. She gave the glass back to the waitress as the man stood, making his way over to her with a swagger to his step. He slid into the booth on the opposite side of her with a wide grin as the waitress departed, his candy apple eyes glinting in the low lighting and making her heart skip an beat involuntarily. 

“So who sent you, Crowley, or my brother?” He drawled casually, cocking an eyebrow at her knowingly. 

Her already racing heart seemed to stop, her eyes widening as she almost choked on her own breath, “W-w-what?”

He snorted sarcastically, rolling his eyes, “Sweetheart, you’ve been sitting in this booth for three hours eyeing me, and I’m not stupid. I see the outline of the blade you have on your ankle, and will put money on the assumption that you have a gun on your hip under that jacket of yours. I can smell a hunter from a hundred miles away. I can also smell the fear on you.” He let a smile creep across his face, his head tilting slightly with affection, “So either you were sent here by one of the people who’ve been looking for me, and they probably scared the shit out of you, or you’re just really, really stupid.”

An audible gulp crawled out of her as she struggled comprehending what was happening. Her body ticked with surprised when he winked at her and his eyes blackened, her reaction that making his shoulder shake and his eye lids crinkle with his giggle. He brought his glass of amber liquid to his lips, taking a sip before letting out a sigh. “So I’m gonna take a chance here and say you work for Crowley, based. on the fact that he’s smart enough to know it’d be hard for me to resist a pretty lady such as yourself.”

Her breathing hitched as her face reddened, a full blown anxiety attack threatening to turn her into a pile of mush as she stared back at the man who had that cocky smile plastered across his mouth as he squinted his eyes at her, “What’s your name, sweetheart?”

She gulped again as she swallowed down the nerves, “Chance.”

A ‘hmph’ was heard out of him as he shook his head for a moment before motioning to the waitress for another round, turning back to look at Chance, he asked, “So what’s he got on ya?”

“What do you mean?” She returned, her brows scrunching together in confusion.

“What’s got you working for him?” He inquired after the waitress brought two more glasses of Whiskey over and disappeared behind the bar silently, “People don’t just hit up the King of Hell for a day job.”

“And what if I did?” She challenged, quirking an eyebrow as she lifted her glass up. He tilted his head down and looked up at her with a bored look, one that called her on her bullshit. 

“Lemme guess, you sold your soul and begged and pleaded when the Hell Hounds came howlin’?” He snorted as he knocked his drink back, chuckling a bit when he saw her shrug and look away, “Thought so.”

Silence fell between the two of them for a few minutes as she gathered her nerves, the feeling of his candy-apple eyes burning through her skin as he watched her. He swiftly swung across the side of the table to sit beside her, his arm crawling across the back of the bench and around her shoulders. She jolted at his sudden movement, her eyes darting to his face as he grinned at her. He blinked once and his eyes flashed black, enticing a small whimper from her throat that tickled him pink. 

“Ya know,  _Chance_ , you can, ya know,  _take a chance_ , and see if I can help you with your little…issue,” He rasped lowly as he moved the hand that had been resting on the top of the table to cup the side of her face, her eyes closing involuntarily as his warm palm engulfed her cheek, “Maybe give you a normal life again?”

The word  _normal_  struck her internally, shaking her from her hypnosis as she retracted her face from his grasp, a disgusted look covering her once serene expression, “I’ve never been  _normal_ , Mr. Winchester. I learned even before Crowley took hold of my future that I should never trust a demon.”

A chuckle rumbled out of the man who was sitting so close to her that she could feel the vibrations from his chest, “Maybe your not as dumb as you look.”

“Wow, such a gentlemen. Bet all the ladies just run after you, huh?” She scoffed, rolling her eyes. 

Dean stuck his bottom lip out and tipped his head from one side to the other in thought, that smirk reappearing as always, “It’s been known to work a couple times.” 

“Pffft,” She snorted in return, focusing on the half-full glass in front of her as she spun it in between her hands before bringing it to her lips.

“Look, all I’m sayin’ is that we can make this a beneficial exchange here, I help you get Crowley off your back, and you help me…get off.”

Liquor flew out past her lips as she spewed it across the table, her eyes widening so much, Dean thought they would surely pop out of her skull if she wasn’t careful. “You’ve  _got_  to be fucking kidding me.”

“Oh, come on, sweetheart,” Dean drawled lowly, that hundred-watt Winchester smile curving his lips as he looked down at her, his eyes flicking from her own irises to her mouth,“Take a  _chance,_ Chance.”

 

* * *

 

She wasn’t sure how it happened, but the next thing she knew she was in the passenger seat of a  _very_  classy Impala, pulling into her hotel parking lot with his hand on her leg. 

‘Maybe this will be easier than I thought,’ She smirked to herself as he put the car in park in front of her room, his face instantly burring into the nape of her neck as soon as the car was off. 

They made their way out of the car and to her door in a tangle of limbs and lips, and he didn’t even notice that he was trapped the moment he set foot into the room. She didn’t even let the sight of his evil irises appear to phase her as he lead her directly to the bed, their clothes falling to the floor as they crawled onto the mattress. 

His mouth molded to hers as he rutted his swollen cock against her thighs, one of his huge hands  pinning her leg to the bed by the back of the knee. She moaned against his lips as the thick head found her moist folds, pushing into her swiftly with one deep thrust.

“Holy shit, babe. Fuck,” He panted as he felt her tight walls convulse around him, adjusting to his girth as she writhed and whimpered. 

After giving her a moment, Dean pulled his aching cock almost all the way out of her before plunging back inside, the thick ridges making her squirm beneath him. 

Her eyes rolled into the back of her head as he set a slow, deep pace that let the rumbles from his growls pour into her as his chest pressed against hers. His shoulders bulged as he held himself above her, their hips meeting as the ground into each other over and over again. 

He kissed her roughly, his hand diving into her hair as he held her close and rocked into her, the drag of his cock through her silky folds driving him insane as he listened to her moan and keen and cry for him. His name sounded angelic on her lips and she tasted like candy, the soprano vocals she was releasing spurring him on and driving him further into the throws of ecstasy.

Minutes turned into hours as they worked each other over, their bodies finally calling for release as he spilled his thick seed inside her as she convulsed around him. The roar he released was demonic, but he muffled it into the burgundy streaks stuck to her neck with sweat, her voice even louder than his own. 

They both fell asleep quickly, Dean’s arm wrapped securely around her. 

 

* * *

 

“Good job, pet,” Crowley cooed saracstically, his brows raised as his voice stirred the two naked sleeping beings on the bed, “Though, I didn’t take you to be the type of girl to actually sleep with the man.”

Embarrassment flushed through Chance’s entire body as she jumped out of the bed and wrapped the sheet around her, her eyes darting between Dean and Crowley as she backed up against the wall. 

Dean looked positively bored as he sat up against the headboard with  a grunt, wiping the sleep from his lids, “Morning to you, too, Crowley. How’s it hanging?”

“A little to the left, thanks for asking,” the King replied unamused, holding his hand out for Chance, “Come, pet, let’s get you home. No need for you to see this.”

“She’s not leaving with you, bitch,” Dean growled back, his eyes flashing black as he made way to stand, wrapping the blanket around his waist, “She’s done with you and so am I.”

Dean flashed her a look of confusion when he attempted to move out of the bed, an invisible force stopping him from leaving the mattress. A smug smirk crossed Crowley’s face as he continued to hold his hand out to her as she crossed past the end of the bed to stand beside him.

“You see, Dean, pet here is very resourceful, I’ve found, and generally can  _always_  find a way to complete a mission, isn’t that right Chancey?”

She didn’t respond as she watched the man on the bed attempt and fail again to get up, a demonic growl echoing through the room with his anger, “Son of a bitch.”

“Are you talking about me, or her ingenious idea of painting a Devil’s Trap under the bed? Or warding the room?” Crowley chuckled. 

“Sorry, Dean,” She sighed finally, moving to find her clothes left thrown across the room, “Looks like you just took the wrong chance with me, huh?”


End file.
